Synthesis and biological evaluation of thioglycosylated porphyrins for an application in photodynamic therapy. |
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Authors: | I Sylvain R Zerrouki R Granet Y M Huang J-F Lagorce M Guilloton J-C Blais P Krausz |
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Affiliation: | Université de Limoges, Laboratoire de Chimie des Substances Naturelles, 123 Avenue Albert Thomas, F-87060, Limoges, France. |
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Abstract: | The aim of this work is the synthesis of a new family of glycosylated porphyrins in which the sugar moieties are linked to the tetrapyrrole ring by a thioglycosidic bond. Two series have been designed. The first one corresponds to meso-aryl porphyrin derivatives. The second one has been obtained from protoporphyrin IX derivatization. Aryl-porphyrins were prepared from tristolyl o- and p-hydroxyporphyrins followed by bromoallylation and thioglycosylation with peracetylated S-glucose, mannose and galactose and deprotection. The other series has been synthesized from protoporphyrin IX dimethylester with a regioselective glycosylation of terminal alkenyl carbon. The UV-visible, NMR and MALDI mass spectra are presented. Photocytotoxicities of the synthesized compounds against K562 chronic leukaemia cell line has been evaluated. |
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